Holiday rentals with outdoor seating in Lewes

Stunning Rustically Modern Downtown Lewes Home

Don’t settle for a hotel! This immaculate three bedroom home in historic downtown Lewes is an ideal blend of classic and modern design. Leave your car in your private space with shops, restaurants, beaches, and the state park a short walk or bike ride away. Enjoy a gourmet kitchen, great room, dining area, & living room space. Lounge in your master bedroom with en-suite bath.The second bedroom (great for families) has double sized bunk beds. The third bedroom has a queen bed and en-suite bath.

A bit of Paradise

Charming end unit secluded in the heart of Lewes. Shady sitting area for viewing the waterfowl & enjoying the peace & quiet. Lewes marina is across the street so is Quest where can rent Kayaks etc. Over the bridge you will enjoy the historic district, town shops, eateries, food market; kiddy park, canal front park; trolley into Rehoboth Beach Henlopen State Park 1 mile; surfing, fishing & nature trails; Bay Beach 1/4 mile w Walk to everything We offer a %15 discount for 7 days or more

Elegant 3-Bedroom Condo in Lewes with Pond Views

You will love this bright open condo, with a vaulted ceiling in the family room.There are gleaming wood floors throughout the main living areas. The large wrap around 3 season room has a large sitting area along with a table for dining with beautiful pond views. The master suite features a large walk in closet and master bath with the guest bedrooms & bathroom on the opposite side. Plantations is a beautiful community with green space, ponds, mature landscaping and walking paths.

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

The Book Nook - A Private Downtown Retreat

In the heart of downtown Milton, you will find a newly renovated guest cottage less than 10 miles to the beach! If you plan on staying local, simply park your car at the designated off-street parking space and travel by foot to the many shops, restaurants, and attractions offered in historic Milton. Whether you're walking the few short blocks to Dogfish Head Brewery or spending an evening at the theater, The Book Nook will serve as the perfect location!

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

For years, we searched for the perfect beach getaway: secluded, tranquil, yet close to attractions. We found it in Beachwalk. Peaceful. Private. Conveniently located at the quiet southern end of Broadkill Beach. While the north side is denser with homes and more crowded, the southern end provides a more private beach experience with far fewer visitors. The ideal beach retreat where it's just you, the sand, and the sea.

Cozy condo in the Villages of Five Points, Lewes

Located in the Villages of Five Points Lewes, east of route 1, our condo is the perfect spot for your weekend gateway or a family beach vacation. Lewes beach is about 3 miles, biking paths and trails that connect to downtown Lewes are in close proximity. Within walking distance from the property enjoy the restaurants, have a splash in the pool in the summer time, or hit the tennis courts for some fun.

Very private and cozy, Country Cottage

You’ll love my place because of the outdoors space and relaxing country feel. The cottage is best for couples. A maximum of two dogs is allowed. Distances from my place to Cape Henlopen Park (9.9miles), Rehoboth Beach (10 miles), Dewey Beach (11 miles). Tanger Outlets (7.8 miles). Please keep in mind that, although the above distances are accurate, driving time may be longer due to seasonal traffic.

Ebb & Flow Beach House - Lewes Bay Beach Retreat

Booking thru Nov 1, 2025. Ebb & Flow Beach House is a 4 bedroom, 3 full bath multi-family retreat with an airy open floor plan. It is tastefully decorated and fully stocked. You will feel relaxed just walking in the door. 5 min walk to the beach. 10-15 minute walk to historic downtown Lewes. Lewes Short Term Rental License R2300082